Amphiphilic organopolysiloxanes having polyester groups and use thereof as emulsifiers or dispersing agents

ABSTRACT

The invention relates to organopolysiloxane copolymers comprising, on average, at least one polyester group bonded to the siloxane via a spacer and, on average, at least one hydrophilic group bonded to the siloxane via a spacer, of the general formula (I):

FIELD OF THE INVENTION

[0001] The present invention relates to amphiphilic organopolysiloxaneshaving polyester groups and to the use thereof as emulsifiers or asdispersing agents.

BACKGROUND OF THE INVENTION

[0002] Organopolysiloxanes having polyester groups have been known for along time. For example, U.S. Pat. No. 5,051,489 describes hydrophobicsilicone polyester waxes that are obtained by esterification of thesilanol groups of siloxanediols with dicarboxylic acids and fatty acids.These waxes are polyesters with a blockwise structure of dialcohols anddicarboxylic acids in which the polysiloxane takes on the function ofthe dialcohol.

[0003] U.S. Pat. No. 5,385,730 discloses mixtures consisting of alow-viscosity silicone oil and a polyester-radical carrying polysiloxanewith a block structure whose polyester radicals are obtained by lactonering-opening. As well as the polyester radicals, these polysiloxanes canalso carry long-chain alkyl radicals. These polysiloxanes arehydrophobic polysiloxanes that can be used as polishes.

[0004] Japanese Patent No. B-3046340 describes polyesters that areobtained by the reaction of terminal aliphatic hydroxyl-group-containingsiloxanediols and dicarboxylic acids, such as adipic acid, andsubsequent reaction with monocarboxylic acids, e.g., also hydroxystearicacid. The silicone polyesters are recommended for use in cosmetics.

[0005] U.S. Pat. No. 5,411,729 describes, inter alia, siliconepolyesters which are obtained by reacting siloxanes carrying lateral orterminal polyether radicals having free OH groups with dicarboxylicacids and polyhydroxy compounds, such as glycerol, and optionally with amonofunctional carboxylic acid. The compounds are used as conditioningagents for hair. U.S. Pat. No. 5,475,125 discloses amphiphilic siliconepolyesters that are obtained by reacting a comb-like polyethersiloxanehaving free OH groups with a dicarboxylic acid and a fatty alcoholethoxylate. These amphiphilic silicone polyesters are recommended asemulsifiers for silicone oil-in-water emulsions.

[0006] From the description of the prior art it is clear that siliconepolyesters of varying structure are known.

[0007] It is possible to differentiate between two basic types ofpolyester. Firstly those which are obtained by polycondensation ofpolyalcohols with dicarboxylic acids, and those which are obtained byself-condensation of hydroxy-functional carboxylic acids or byring-opening reaction of corresponding lactones.

[0008] The first-mentioned type has a block structure if the polyalcoholis a diol. Here, the polysiloxane can take on the function of the diol,as described in U.S. Pat. No. 5,051,489 or Japanese Patent No.B-3046340. The siloxanediol can carry silanol-like OH groups, whichleads to readily hydrolyzable Si—O bonds, or hydroxyalkyl groups, whichproduce hydrolysis-resistant Si—C bonds.

[0009] However, the siloxane can also carry more than 2 OH groups, asdescribed in U.S. Pat. No. 5,475,125. A disadvantage of the siliconepolyesters prepared in this way is that the dicarboxylic acid used canact as a bridge between two silicone polyethers and triggerscrosslinking reactions which are difficult to control and which may leadto complete gelation of the product.

[0010] U.S. Pat. No. 5,411,729 also discloses silicone polyesters which,as well as the polyhydroxy-functional siloxane, additionally contain anorganic polyhydroxy compound as a building block. However, in this casetoo, crosslinking reactions are to be expected

[0011] Silicone polyesters can be prepared in a more controlled mannerby ring-opening reactions of lactones with hydroxy-functional siloxanes,see, for example, U.S. Pat. No. 5,385,730. In this way, crosslinkingreactions can be completely avoided.

[0012] In principle, polyester siloxanes can be divided into amphiphilicand nonamphiphilic types. Siloxanes, which carry only polyesterradicals, are usually hydrophobic and do not exhibit interface activitybetween a hydrophilic and a hydrophobic phase. Polyester siloxanes thatalso carry hydrophilic groups, such as, for example, polyether radicalsare, by contrast interface-active and can be used, for example, asemulsifiers. This is disclosed, for example, in U.S. Pat. Nos. 5,411,729and 5,475,125.

[0013] The use of amphiphilically modified polysiloxanes, in particularpolyether-modified polysiloxanes, as emulsifiers and dispersing agentshas been known for a long time. The use of interface-active siliconepolyethers in emulsifier systems is described in detail, for example, inU.S. Pat. No. 4,988,504. Polysiloxane compounds are proposed whichconsist of

[0014] a) units of the formula

R₂SiO_(2/2),

[0015] wherein

[0016]  R=hydrogen or a substituted or unsubstituted hydrocarbon radicalhaving 1 to 12 carbon atoms,

[0017] b) units of the formula

RR¹SiO_(2/2),

[0018] wherein

[0019]  R¹=polyalkylene ether of the formula

[0020]  —R³ _(a) 13 (OR²)_(n)—OR⁴, in which

[0021]  R²═—CH₂CH₂—,

[0022]  R³=substituted or unsubstituted alkylene group having 1 to 20carbon atoms,

[0023]  R⁴═R,

[0024]  n has a value from 5 to 20, and

[0025]  a is 0 or 1, and

[0026] c) end members of the siloxane chain, where the molecular weightof component a) should be about 25,000 to 35,000. These emulsifiers withlateral polyoxyalkylene groups should bring about improved propertiesfor antiperspirant sticks with regard to stability and low wax content.

[0027] European Patent B-0 407 089 relates to a transparentwater-in-silicone oil emulsion, suitable for external application tomammallain skin or hair, comprising, in addition to water.

[0028] i. 1 to 50% by weight of a volatile polydimethylsiloxane;

[0029] ii. 0.1 to 20% by weight of a silicone surfactant ingredientcomprising a polymer of dimethylpolysiloxane with polyoxyethylene and/orpolyoxypropylene sidechains with a molecular weight of from 10,000 to50,000 and the structural formula:

[0030]  in which

[0031] R═—H or

[0032] a has a value from 9 to 115,

[0033] b has a value from 0 to 50,

[0034] x has a value from 133 to 673, and

[0035] y has a value from 25 to 0.25; and

[0036] iii. 1 to 50% by weight of a transparency-imparting agent, whichis at least one polyhydric alcohol.

[0037] European Patent B-0 176 844 discloses the use of polysiloxaneswith polyether and long-chain alkyl radicals added on in a comb-likemanner as emulsifiers for the preparation of W/O emulsions, the oilyphase of which consists of silicone oil, or comprises this. EuropeanPatent A-0 819 426 describes the use of terminally modifiedpolyethersiloxanes as emulsifiers in W/O emulsions.

[0038] The disadvantage of prior art polyether-modified polysiloxanesdescribed here is, however, that when the polyether-modifiedpolysiloxanes are used as emulsifiers in W/O emulsions, undesirably highemulsion viscosities, especially in the case of emulsions with a highwater phase content, are achieved.

SUMMARY OF THE INVENTION

[0039] An object of the present invention is therefore to provideemulsifiers for cosmetic W/O emulsions that have a low viscosity.

[0040] According to the present invention, this object is achieved bythe use of organopolysiloxane copolymers comprising, on average, atleast one polyester group bonded to the siloxane via a spacer and, onaverage, at least one hydrophilic group bonded to the siloxane via aspacer.

[0041] The present invention therefore provides organopolysiloxanecopolymers comprising, on average, at least one polyester group bondedto the siloxane via a spacer and, on average, at least one hydrophilicgroup bonded to the siloxane via a spacer, of the general formula (I):

[0042] in which

[0043] R¹ are identical or different and are alkyl radicals having 1 to30 carbon atoms or phenyl radicals,

[0044] R² independently of one another are R¹, —A—R³ or —B—R⁴ in which

[0045] —A— is a divalent alkyleneoxy group having 3 to 24 carbon atomswhich is optionally branched and/or can contain double bonds,

[0046] and/or is a divalent polyoxyalkylene group of the general averageformula

—R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—

[0047] in which

[0048] q=1 to 100,

[0049] r=0 to 100,

[0050] s=0 to 100,

[0051] R⁵ is a divalent alkyleneoxy group having 1 to 24 carbon atomswhich is optionally branched and/or can contain double bonds,

[0052] R³ is a polyester radical of the general formula

[0053]  in which

[0054] t is integers in the range from 1 to 10, and [—(O═C)—S—O—] is thefragment of a corresponding hydroxycarboxylic acid HO—(O═C)—S—OH, inwhich

[0055] —S— is an optionally branched and/or double-bond-containingalkylene radical having 5 to 30 carbon atoms, with the proviso that atleast 5 carbon atoms are between the carboxyl group [HO—C(O)—] and thehydroxyl group [—OH];

[0056] —B— acts as a spacer between siloxane backbone and the radical R⁴and is of a type known from the prior art for hydrophilically modifiedsiloxanes,

[0057] R⁴ is a hydrophilic radical of the general average formula

—R⁶—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—R

[0058]  in which

[0059] q=1 to 100,

[0060] r=0 to 100,

[0061] s=0 to 100,

[0062] R⁶ is a divalent alkylene or alkyleneoxy group having 1 to 24carbon atoms which is optionally branched and/or can contain doublebonds;

[0063] R⁷ is a hydrogen atom, alkyl or acyl radical having 1 to 20carbon atoms, or

[0064] R⁴ is a polyhydroxyorganyl radical, in particular a glycerol,polyglycerol, sugar or sugar derivative radical, a polyvinyl alcoholradical, a carboxylate, sulfate or phosphate radical, an ammoniumradical or an amphoteric betaine or amphoglycinate radical,

[0065] a has a value from 1 to 1000, preferably 5 to 500, in particular10 to 150, and

[0066] b has a value from 0 to 10, preferably b is <2, with the provisothat, on statistical average, at least in each case one radical R²=—A—R³and R²=—B—R⁴ is present, or in the case where no radical —B—R⁴ ispresent, at least one radical R²=—A—R³ is present in which —A— is adivalent polyoxyalkylene group of the above-described general averageformula

—R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—.

[0067] A preferred embodiment of the present invention isorganopolysiloxane copolymers of the general formula (I) in which thefragment [—(O═C)—S—O—]_(t) corresponds to the radical of12-hydroxystearic acid or of ricinoleic acid and t is between 2 and 5.

[0068] A further preferred embodiment of the present invention isorganopolysiloxane copolymers of the general formula (I) in which thehydrophilic radical is selected from the group of polyethers.

[0069] The present invention further provides for the use of thepolysiloxane copolymers of the general formula (I) as emulsifiers,optionally with co-use of further emulsifiers, for the preparation oflow-viscosity W/O emulsions with a high content of disperse phase.

[0070] The present application further provides processes for thepreparation of the compounds according to the present invention, whichcomprise adding on the polyester radicals either by hydrosilylation ofpolyesters carrying double bonds to polyhydrogensiloxanes, or byesterification of OH-functional polysiloxanes with polyesters carryingfree carboxyl groups, and the hydrophilic radicals by processes knownfrom the prior art to the polysiloxane. The spacers (B) are the radicalsknown from the prior art, such as C₁₋₂₄alkylene radicals, which mayoptionally be branched, and may optionally contain multiple bonds orheteroatoms, such as, in particular, oxygen atoms, and/or functionalgroups, such as, in particular, hydroxyl groups.

DETAILED DESCRIPTION OF THE INVENTION

[0071] As stated above, the present invention provides amphiphilicorganopolysiloxanes having polyester groups that are useful asemulsifiers or dispersing agents. The inventive amphiphilicpolysiloxanes are organopolysiloxane copolymers comprising, on average,at least one polyester group bonded to the siloxane via a spacer and, onaverage, at least one hydrophilic group bonded to the siloxane via aspacer, of the general formula (I):

[0072] in which the variables R¹, R², a and b are as defined above.

[0073] The compounds of the general formula (I) are used in amounts offrom about 0.5 to about 4% by weight, based on the total formulation,for the preparation of aqueous dispersions and emulsions, in particularfor the preparation of W/O emulsions for cosmetic purposes, where theformulation constituents known for these fields of application, such asoil components, fats and waxes, polyols, active ingredients, such asvitamins, fruit acids and amino acids, such as creatine, perfume oils,dyes, pigments, UV filters, electrolytes, are co-used in the customaryamounts.

[0074] Examples of compounds according to the present invention are:

[0075] The compounds of formula (I) are prepared by adding on thepolyester radicals either by hydrosilylation of polyesters carryingdouble bonds to polyhydrogensiloxanes, or by esterification ofOH-functional polysiloxanes with polyesters carrying free carboxylgroups, and the hydrophilic radicals.

[0076] The examples below illustrate the present invention.

EXAMPLE 1

[0077] 71.8 g of polyhydroxystearic acid (n=2, acid number=93.7 mg ofKOH/g) were melted, homogenized and, together with 112.2 g of a doublyterminally modified polyether-siloxane (siloxane chain length N=10),molecular weight of the polyether (100% polyethylene glycol)=600 g/mol,OH number of the polyether-siloxane: 60 mg of KOH/g) and 120 g oftoluene, were transferred to a 500 ml three-necked flask fitted withwater separator, stirrer and thermometer. 0.55 g of methanesulfonic acidwere added and the mixture was heated at 125° C. for 6 h with stirring.The solvent was then removed on a rotary evaporator at 80° to 100° C.

[0078] This gave a clear, brownish liquid. The conversion, determined bymeans of the final value of the acid number, was about 99%.

EXAMPLES 2 to 4

[0079] TABLE 1 Experimental details for examples 2 to 4Polyether-siloxane: Siloxane chain length N, Molecular weight ofpolyether MW [g/mol], Initial wt Initial wt of Initial wt of OH numberof of polyether- polyhydroxy- methane- Initial wt of Examplepolyethersiloxane siloxane stearic acid sulfonic acid toluene No. [mg ofKOH/g] [g] [g] [g] [g] 2 N = 10, 98.2 93.5 0.58 120 MW = 400, OH number= 80 3 N = 20, 114.1 80.1 0.58 120 MW = 400, OH number = 59 4 N = 80,154.3 36.7 0.57 120 MW = 400, OH number = 93.7

[0080] Applications Section

EXAMPLE 5

[0081] Emulsion No. Phase (Ingredient data in %) 1 2 3 4 5 6 7 8 9 AEmulsifier from — 2 — 1.5 1.5 — — — — example 2 Emulsifier from 2 — 2 —— 1.5 1.5 — — example 3 Cetyl Dimethicone — — — — — — — 2 2 Copolyol(ABIL EM 90) Diisostearoyl — — — 0.5 0.5 0.5 0.5 — — Polyglyceryl- 3Dimer Dilinoleate (ISOLAN PDI) Microcrys-talline Wax — — — — — — 0.25 —— Castor Wax — — — — — — 0.25 — — Mineral Oil — 23 23 23 — — 8 23 7.6Ethylhexyl Stearate 23 — — — 23 23 8 — 7.7 Caprylic/Capric — — — — — 8 —7.7 Triglyceride B Glycerol 2.45 2.45 2.45 2.45 2.45 2.45 3.35 2.4542.45 Bronopol 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 MagnesiumSulfate 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Heptahydrate Water 72 72 7272 72 72 68 72 72 Emulsion viscosity V1 = 9 V1 = 6 V1 = 10 V1 = 11 V1 =8 V1 = 8 V1 = 12 V1 = 36 V1 = 52 [Pas] after 2 days at V1 = 7 V2 = 6 V2= 7 V2 = 10 V2 = 7 V2 = 9 V2 = 13 V2 = 22 V2 = 28 room temperature (V 1)and after 2 months at room temperature (V2)

[0082] The emulsions were prepared by adding the components of phase Bto the components of phase A with stirring and then homogenizing themixture for 1 min. with a hand rotor-stator mixer.

[0083] In the case of emulsion 7, the components of phase A have to beheated to about 80° C. so that the wax-like components (microcrystallinewax and castor wax) are molten. The oil phase can then be cooled againto room temperature and the procedure described above was followed.

[0084] Emulsions 8 and 9 are comparison emulsions. It can be seen from adirect comparison of emulsion 2 with comparison emulsion 8, or ofemulsion 3 with comparison emulsion 9, that using the compoundsaccording to the present invention as emulsifiers, a significantly loweremulsion viscosity is achieved: 6 compared with 36 and 10 compared with52 Pas, which also, in contrast to the comparison emulsions, is stableover the storage period of at least 2 months, whereas in the case ofcomparison emulsion 8, the viscosity decreases significantly from 36 to22 and in the case of comparison emulsion 9 from 52 to 28 Pas.

[0085] Emulsions 4 to 7 further show that the compounds according to theinvention also lead to the desirably low emulsion viscosities incombination with conventional emulsifiers.

[0086] While the present invention has been particularly shown anddescribed with respect to preferred embodiments thereof, it will beunderstood by those skilled in the art that the foregoing and otherchanges in forms and details may be made without departing from thespirit and scope of the present invention. It is therefore intended thatthe present invention not be limited to the exact forms and detailsdescribed and illustrated, but fall within the scope of the appendedclaims.

1. An organopolysiloxane copolymer comprising, on average, at least onepolyester group bonded to a siloxane via a spacer and, on average, atleast one hydrophilic group bonded to the siloxane via a spacer, of thegeneral formula (I):

in which R¹ are identical or different and are alkyl radicals having 1to 30 carbon atoms or phenyl radicals, R² independently of one anotherare R¹, —A—R³ or —B—R⁴ in which —A— is a divalent alkyleneoxy grouphaving 3 to 24 carbon atoms, which is optionally branched and/or cancontain double bonds, and/or is a divalent polyoxyalkylene group of thegeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—in whichq=1 to 100, r=0 to 100, s=0 to 100, R⁵ is a divalent alkyleneoxy grouphaving 1 to 24 carbon atoms, which is optionally branched and/or cancontain double bonds, R³ is a polyester radical of the general formula

in which t is integers in the range from 1 to 10, and [—(O═C)S—O—] isthe fragment of a corresponding hydroxycarboxylic acid HO—(O═C)—S—OH, in which —S— is an optionally branched and/or double-bond-containingalkylene radical having 5 to 30 carbon atoms, with the proviso that atleast 5 carbon atoms are between the carboxyl group [HO—C(O)—] and thehydroxyl group [—OH]; —B— acts as a spacer between siloxane backbone andthe radical R⁴, R⁴ is a hydrophilic radical of the general averageformula —R⁶—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—R⁷ in which q=1 to 100,r=0 to 100, s=0 to 100, R⁶ is a divalent alkylene or alkyleneoxy grouphaving 1 to 24 carbon atoms which is optionally branched and/or cancontain double bonds; R⁷ is a hydrogen atom, alkyl or acyl radicalhaving 1 to 20 carbon atoms, or R⁴ is a polyhydroxyorganyl radical, inparticular a glycerol, polyglycerol, sugar or sugar derivative radical,a polyvinyl alcohol radical, a carboxylate, sulfate or phosphateradical, an ammonium radical or an amphoteric betaine or amphoglycinateradical, a has a value from 1 to 1000, and b has a value from 0 to 10with the proviso that, on statistical average, at least in each case oneradical R²=—A—R³ and R²=—B—R⁴ is present, or in the case where noradical —B—R⁴ is present, at least one radical R²=—A—R³ is present inwhich —A— is a divalent polyoxyalkylene group of the above-describedgeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—.
 2. Theorganopolysiloxane copolymer as claimed in claim 1, wherein the fragment[—(O═C)—S—O—]_(t) corresponds to the radical of 12-hydroxystearic acidor of ricinoleic acid and t is between 2 and
 5. 3. Theorganopolysiloxane copolymer as claimed in claim 1, wherein thehydrophilic radical R⁴ is a radical selected from the group consistingof polyethers, polyglycerol, polyvinyl alcohol, sugar and sugarderivatives.
 4. The organopolysiloxane copolymer as claimed in claim 1,wherein b=0 and a=10 to
 150. 5. A process for the preparation of acompound of general formula (I)

in which R¹ are identical or different and are alkyl radicals having 1to 30 carbon atoms or phenyl radicals, R² independently of one anotherare R¹, —A—R³ or —B—R⁴ in which —A— is a divalent alkyleneoxy grouphaving 3 to 24 carbon atoms, which is optionally branched and/or cancontain double bonds, and/or is a divalent polyoxyalkylene group of thegeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—  inwhich q=1 to 100, r=0 to 100, s=0 to 100, R⁵ is a divalent alkyleneoxygroup having 1 to 24 carbon atoms, which is optionally branched and/orcan contain double bonds, R³ is a polyester radical of the generalformula

 in which t is integers in the range from 1 to 10, and [—(O═C)—S—O—] isthe fragment of a corresponding hydroxycarboxylic acid HO—(O═C)—S—OH, in which —S— is an optionally branched and/or double-bond-containingalkylene radical having 5 to 30 carbon atoms, with the proviso that atleast 5 carbon atoms are between the carboxyl group [HO—C(O)—] and thehydroxyl group [—OH]; —B— acts as a spacer between siloxane backbone andthe radical R⁴, R⁴ is a hydrophilic radical of the general averageformula —R⁶—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—R⁷ in which q=1 to 100,r=0 to 100, s=0 to 100, R⁶ is a divalent alkylene or alkyleneoxy grouphaving 1 to 24 carbon atoms which is optionally branched and/or cancontain double bonds; R⁷ is a hydrogen atom, alkyl or acyl radicalhaving 1 to 20 carbon atoms, or R⁴ is a polyhydroxyorganyl radical, inparticular a glycerol, polyglycerol, sugar or sugar derivative radical,a polyvinyl alcohol radical, a carboxylate, sulfate or phosphateradical, an ammonium radical or an amphoteric betaine or amphoglycinateradical, a has a value from 1 to 1000, and b has a value from 0 to 10with the proviso that, on statistical average, at least in each case oneradical R²=—A—R³ and R²=—B—R⁴ is present, or in the case where noradical —B—R⁴ is present, at least one radical R²=—A—R³ is present inwhich —A— is a divalent polyoxyalkylene group of the above-describedgeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—, whichcomprises adding on polyester radicals either by hydrosilylation of apolyester carrying a double bond to a polyhydrogensiloxane, or byesterification of an OH-functional polysiloxane with a polyestercarrying a free carboxyl group.
 6. The method of claim 5, wherein thefragment [—(O═C)—S—O—]_(t) corresponds to the radical of12-hydroxystearic acid or of ricinoleic acid and t is between 2 and 5.7. The method of claim 5, wherein the hydrophilic radical R⁴ is aradical selected from the group consisting of polyethers, polyglycerol,polyvinyl alcohol, sugar and sugar derivatives.
 8. The method of claim5, wherein b=0 and a=10 to
 150. 9. A dispersion or emulsion comprisingat least one of compound of general formula (I)

in which R¹ are identical or different and are alkyl radicals having 1to 30 carbon atoms or phenyl radicals, R² independently of one anotherare R¹, —A—R³ or —B—R⁴ in which —A— is a divalent alkyleneoxy grouphaving 3 to 24 carbon atoms, which is optionally branched and/or cancontain double bonds, and/or is a divalent polyoxyalkylene group of thegeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—  inwhich q=1 to 100, r=0 to 100, s=0 to 100, R⁵ is a divalent alkyleneoxygroup having 1 to 24 carbon atoms, which is optionally branched and/orcan contain double bonds, R³ is a polyester radical of the generalformula

 in which t is integers in the range from 1 to 10, and [—(O═C)—S—O—] isthe fragment of a corresponding hydroxycarboxylic acid HO—(O═C)—S—OH, inwhich —S— is an optionally branched and/or double-bond-containingalkylene radical having 5 to 30 carbon atoms, with the proviso that atleast 5 carbon atoms are between the carboxyl group [HO—C(O)—] and thehydroxyl group [—OH]; —B— acts as a spacer between siloxane backbone andthe radical R⁴, R⁴ is a hydrophilic radical of the general averageformula —R⁶—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—R⁷  in which q=1 to 100,r=0 to 100, s=0 to 100, R⁶ is a divalent alkylene or alkyleneoxy grouphaving 1 to 24 carbon atoms which is optionally branched and/or cancontain double bonds; R⁷ is a hydrogen atom, alkyl or acyl radicalhaving 1 to 20 carbon atoms, or R⁴ is a polyhydroxyorganyl radical, inparticular a glycerol, polyglycerol, sugar or sugar derivative radical,a polyvinyl alcohol radical, a carboxylate, sulfate or phosphateradical, an ammonium radical or an amphoteric betaine or amphoglycinateradical, a has a value from 1 to 1000, and b has a value from 0 to 10with the proviso that, on statistical average, at least in each case oneradical R²=—A—R³ and R²=—B—R⁴ is present, or in the case where noradical —B—R⁴ is present, at least one radical R²=—A—R³ is present inwhich —A— is a divalent polyoxyalkylene group of the above-describedgeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—. 10.The dispersion or emulsion of claim 9 further comprising additionalemulsifiers which when used in conjunction with the compound of generalformula (I) provide a low-viscosity W/O emulsion having a high contentof a dispersed phase.
 11. The dispersion or emulsion of claim 9, whereinthe fragment [—(O═C)—S—O—]_(t) corresponds to the radical of12-hydroxystearic acid or of ricinoleic acid and t is between 2 and 5.12. The dispersion or emulsion of claim 9, wherein the hydrophilicradical R⁴ is a radical selected from the group consisting ofpolyethers, polyglycerol, polyvinyl alcohol, sugar and sugarderivatives.
 13. The dispersion or emulsion of claim 9, wherein b=0 anda=10 to
 150. 14. A cosmetic W/O emulsion comprising 0.5 to 4% by weight,based on the total formulation, of at least one of compound of generalformula (I)

in which R¹ are identical or different and are alkyl radicals having 1to 30 carbon atoms or phenyl radicals, R² independently of one anotherare R¹, —A—R³ or —B—R⁴ in which —A— is a divalent alkyleneoxy grouphaving 3 to 24 carbon atoms, which is optionally branched and/or cancontain double bonds, and/or is a divalent polyoxyalkylene group of thegeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—  inwhich q=1 to 100, r=0 to 100, s=0 to 100, R⁵ is a divalent alkyleneoxygroup having 1 to 24 carbon atoms, which is optionally branched and/orcan contain double bonds, R³ is a polyester radical of the generalformula

 in which t is integers in the range from 1 to 10, and [—(O═C)—S—O—] isthe fragment of a corresponding hydroxycarboxylic acid HO—(O═C)—S—OH, in which —S— is an optionally branched and/or double-bond-containingalkylene radical having 5 to 30 carbon atoms, with the proviso that atleast 5 carbon atoms are between the carboxyl group [HO—C(O)—] and thehydroxyl group [—OH]; —B— acts as a spacer between siloxane backbone andthe radical R⁴, R⁴ is a hydrophilic radical of the general averageformula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—R⁷  in which q=1 to 100,r=0 to 100, s=0 to 100, R³is a divalent alkylene or alkyleneoxy grouphaving 1 to 24 carbon atoms which is optionally branched and/or cancontain double bonds; R7 is a hydrogen atom, alkyl or acyl radicalhaving 1 to 20 carbon atoms, or R⁴ is a polyhydroxyorganyl radical, inparticular a glycerol, polyglycerol, sugar or sugar derivative radical,a polyvinyl alcohol radical, a carboxylate, sulfate or phosphateradical, an ammonium radical or an amphoteric betaine or amphoglycinateradical, a has a value from 1 to 1000, and b has a value from 0 to 10with the proviso that, on statistical average, at least in each case oneradical R²=—A—R³ and R²=—B—R⁴ is present, or in the case where noradical —B—R⁴ is present, at least one radical R²=—A—R³ is present inwhich —A— is a divalent polyoxyalkylene group of the above-describedgeneral average formula —R⁵—(C₂H₄O)_(q)—(C₃H₆O)_(r)—(C₄H₈O)_(s)—. 15.The cosmetic W/O emulsion of claim 14, wherein the fragment[—(O═C)—S—O—]_(t) corresponds to the radical of 12-hydroxystearic acidor of ricinoleic acid and t is between 2 and
 5. 16. The cosmetic W/Oemulsion of claim 14, wherein the hydrophilic radical R⁴ is a radicalselected from the group consisting of polyethers, polyglycerol,polyvinyl alcohol, sugar and sugar derivatives.
 17. The cosmetic W/Oemulsion of claim 14, wherein b=0 and a=10 to 150.